What if you'd held MSTR?
A $1,000 investment in Strategy Inc (MSTR) at the month-end close of 1998-06 would be worth $7,381 at the close of 2026-08 — +638.1% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $6,798.
Your scenario
Result
If you'd bought $1,000 at the start of each year
Value of $1,000 invested on January 1 of each year, held to 2026-08, dividends included.
Every year, $1,000 from 1998
| Year | Value of $1,000 | Year return |
|---|---|---|
| 1998 | $1,000 | — |
| 1999 | $6,667 | +566.7% |
| 2000 | $603 | -91.0% |
| 2001 | $244 | -59.5% |
| 2002 | $95.87 | -60.8% |
| 2003 | $333 | +247.5% |
| 2004 | $383 | +14.8% |
| 2005 | $525 | +37.2% |
| 2006 | $724 | +37.9% |
| 2007 | $604 | -16.6% |
| 2008 | $236 | -61.0% |
| 2009 | $597 | +153.2% |
| 2010 | $543 | -9.1% |
| 2011 | $688 | +26.7% |
| 2012 | $593 | -13.8% |
| 2013 | $789 | +33.0% |
| 2014 | $1,031 | +30.7% |
| 2015 | $1,138 | +10.4% |
| 2016 | $1,253 | +10.1% |
| 2017 | $834 | -33.5% |
| 2018 | $811 | -2.7% |
| 2019 | $906 | +11.6% |
| 2020 | $2,467 | +172.4% |
| 2021 | $3,457 | +40.1% |
| 2022 | $899 | -74.0% |
| 2023 | $4,010 | +346.2% |
| 2024 | $18,389 | +358.5% |
| 2025 | $9,648 | -47.5% |
| 2026 | $6,619 | -31.4% |
Best and worst month-end to buy
The best single month-end close to have bought MSTR was 2002-06 ($0.50): $1,000 then is $208,500 today. The worst was 2025-06 ($404): $1,000 then is $258.
FAQ
What would $1,000 in MSTR be worth today?
A $1,000 investment in Strategy Inc (MSTR) at the start of 1998 would be worth about $7,381 today, a total return of +638.1%. Dividends are reinvested in these figures.
What were the best and worst years for MSTR?
Strategy Inc (MSTR)'s strongest calendar year since 1998 was 1999, a +566.7% return — $1,000 held through that year became about $6,667 by year-end. Its weakest year was 2000, at -91.0%.
Does the calculator include dividends and splits?
Yes where available. Prices are adjusted for both stock splits and reinvested dividends (total return), the same measure brokerages use.
How much would $100 per month in MSTR have grown?
Investing $100 at the end of every month since 1998-06 would have grown to about $433,677 on $33,900 invested.
Did MSTR beat the S&P 500?
Over the same period, $1,000 in the S&P 500 index would be worth $6,798. MSTR beat the S&P 500 by +8.6% in total return.
Is this investment advice?
No. What If I'd Held is an entertainment and education tool. Every number is a historical calculation, not a prediction, and past performance never guarantees future results.
Methodology
Strategy Inc (MSTR) historical total-return data from 1998-06 to 2026-08, reduced to month-end closes for the tables above.
Returns use adjusted close prices from Yahoo Finance historical data — adjusted for stock splits and reinvested dividends — the same convention used by major brokerages. A "year" scenario invests $1,000 at the prior December's month-end close and values it at the latest available month-end close. Non-USD amounts are converted at historical month-end exchange rates (Yahoo Finance): to USD on the buy date and back to your currency at the latest rate, so the return reflects the currency move as well as the asset.
Month-end resolution means intra-month extremes are not captured in tables; the calculator uses exact trading-day closes where daily data is available. Figures ignore taxes, fees, and the currency effects of non-USD listings. History is not a forecast. What If I'd Held is entertainment, not investment advice.
What if you'd held…
Data: adjusted close prices via Yahoo Finance. As of 2026-08. Not financial advice.